Acetone → HCID 57428842, compound

HRID 2267385Notes

Reaction equation

HRID 2267385 reaction equation
[S-:1][C:2]#[N:3].[NH4+:4].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6].[F:17][C:18]1[CH:25]=[CH:24][C:21](NC)=[CH:20][CH:19]=1.[CH3:26]C(C)=O>>[F:17][C:18]1[CH:25]=[CH:24][C:21]([N:4]([CH3:26])[C:2]([NH:3][C:12](=[O:13])[C:11]2[CH:15]=[CH:16][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=2)=[S:1])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 180Acetone2×HCID 85024-Nitrobenzoyl chlorideHCID 15666Ammonium thiocyanateHCID 680244-Fluoro-N-methylaniline

Product 1

HCID 57428842HCID 57428842, compound

Procedure

A solution of 3.8 g (50 mmol) of ammonium thiocyanate in 100 mL of acetone was treated with a solution of 8.4 g (45 mmol) of 4-nitrobenzoyl chloride in 50 mL of acetone and the reaction solution was heated at reflux for 15 min. The reaction solution was removed from heating and 5.2 g (41 mmol) of 4-fluoro-N-methylaniline was added at such a rate as to maintain reflux, then heating was renewed for 15 min. The reaction mixture was poured onto 400 g of ice to give an orange oil that separated and solidified on standing. The solid was collected by filtration, washed with water and dried to give 1-(4-fluorophenyl)-1-methyl-3-(4-nitrobenzoyl)thiourea which was suspended in 500 mL of MeOH and treated with 2 mL (64 mmol) of hydrazine for 18 h. The byproduct 4-nitrobenzohydrazide was removed by filtration and the organic solvent was removed from the product in vacuo. The residue was dissolved in 500 mL of 8:1:1 (v/v/v) EtOAc/CHCl3/MeOH, washed thrice with 10% (w/v) aqueous HCl, then dried over a mixture of solid MgSO4 and solid Na2CO3, filtered and concentrated to give the desired compound. MS (M+H)+ 185.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureat reflux for 15 min
  3. customThe reaction solution was removed
  4. temperaturefrom heating
  5. temperatureto maintain
  6. temperaturereflux
  7. temperatureheating
  8. customto give an orange oil
  9. customthat separated
  10. filtrationThe solid was collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-538b746bbc494956add2e313470a057b
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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